(2S)-2-{[(1R,4S,7S,13S,16S,19R,24R,27S,30S,33S,40R)-40-(2-aminoacetamido)-4,27,33-tris(3-carbamimidamidopropyl)-13-(carboxymethyl)-16-(hydroxymethyl)-30-[(4-hydroxyphenyl)methyl]-3,6,12,15,18,26,29,32,35,41-decaoxo-21,22,37,38-tetrathia-2,5,11,14,17,25,28,31,34,42-decaazatricyclo[17.16.7.0^{7,11}]dotetracontan-24-yl]formamido}-5-carbamimidamidopentanoic acid

ID: ALA1836968

Chembl Id: CHEMBL1836968

PubChem CID: 56679246

Max Phase: Preclinical

Molecular Formula: C59H95N25O18S4

Molecular Weight: 1570.83

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@H](NC(=O)[C@@H]1CSSC[C@@H]2NC(=O)[C@@H](NC(=O)CN)CSSC[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]3CCCN3C(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC2=O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc2ccc(O)cc2)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1)C(=O)O

Standard InChI:  InChI=1S/C59H95N25O18S4/c60-22-42(87)73-37-24-103-104-25-38-50(96)75-30(6-1-15-69-56(61)62)44(90)78-34(20-28-11-13-29(86)14-12-28)47(93)74-31(7-2-16-70-57(63)64)45(91)82-39(51(97)77-33(55(101)102)9-4-18-72-59(67)68)26-105-106-27-40(83-49(37)95)52(98)80-36(23-85)48(94)79-35(21-43(88)89)54(100)84-19-5-10-41(84)53(99)76-32(46(92)81-38)8-3-17-71-58(65)66/h11-14,30-41,85-86H,1-10,15-27,60H2,(H,73,87)(H,74,93)(H,75,96)(H,76,99)(H,77,97)(H,78,90)(H,79,94)(H,80,98)(H,81,92)(H,82,91)(H,83,95)(H,88,89)(H,101,102)(H4,61,62,69)(H4,63,64,70)(H4,65,66,71)(H4,67,68,72)/t30-,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-/m0/s1

Standard InChI Key:  XLQOVPAFVSHLGV-VFWMWCIBSA-N

Alternative Forms

1. Parent:

   

   ALA1836968

   H-Gly-Cys(1)-Cys(2)-Ser-Asp-Pro-Arg-Cys(1)-Arg-Tyr-Arg-Cys(2)-Arg-OH

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1570.83

Molecular Weight (Monoisotopic): 1569.6170

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Halai R, Callaghan B, Daly NL, Clark RJ, Adams DJ, Craik DJ..  (2011)  Effects of cyclization on stability, structure, and activity of α-conotoxin RgIA at the α9α10 nicotinic acetylcholine receptor and GABA(B) receptor.,  54  (19): [PMID:21888386] [10.1021/jm201060r]

2. Chhabra S, Belgi A, Bartels P, van Lierop BJ, Robinson SD, Kompella SN, Hung A, Callaghan BP, Adams DJ, Robinson AJ, Norton RS..  (2014)  Dicarba analogues of α-conotoxin RgIA. Structure, stability, and activity at potential pain targets.,  57  (23): [PMID:25393758] [10.1021/jm501126u]

3. Liang J, Tae HS, Xu X, Jiang T, Adams DJ, Yu R..  (2020)  Dimerization of α-Conotoxins as a Strategy to Enhance the Inhibition of the Human α7 and α9α10 Nicotinic Acetylcholine Receptors.,  63  (6): [PMID:32101438] [10.1021/acs.jmedchem.9b01536]

4. Zheng N, Christensen SB, Dowell C, Purushottam L, Skalicky JJ, McIntosh JM, Chou DH..  (2021)  Discovery of Methylene Thioacetal-Incorporated α-RgIA Analogues as Potent and Stable Antagonists of the Human α9α10 Nicotinic Acetylcholine Receptor for the Treatment of Neuropathic Pain.,  64  (13.0): [PMID:34161094] [10.1021/acs.jmedchem.1c00802]

Source

Source(1):

• Scientific Literature